Vintage homes for sale & real estate in Connecticut, CT

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ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Set on 1.57 picturesque acres this beautifully reimagined farmhouse colonial pairs timeless New England character with a comprehensive top-to-bottom renovation. From the original windows and hand-laid stone floors to the reclaimed shiplap walls and solid wood doors, every detail honors the home's 1959 roots with modern systems and design. A recent full-scale renovation touched virtually every system in the home - HVAC, tankless water heater, plumbing, electrical, kitchen, baths, flooring, and millwork -move in with confidence and none of the guesswork of an older home. The main level offers the open, connected layout today's buyers are searching for: a flowing family, living, and dining spa

$1,399,900

4 beds2.5 baths3,768 sq ft

235 Newtown Tpke, Weston, CT 06883

Original windows • Picturesque acres • 1.57 acre lot

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
An incredible opportunity to own in Stamford! Located at 21 W. Main Street, this spacious 2 bedroom, 1 bath condo offers 860 sq ft of comfortable living space with beautiful views of Downtown Stamford. Inside, you'll find a bright and functional layout featuring generously sized rooms, an in-unit washer and dryer, and the added benefit of an energy-efficient tankless water heater. Enjoy the convenience of two dedicated parking spaces, a rare and valuable feature for city living. Situated on the fourth floor of a walk-up building, this home offers privacy, natural light, and elevated city views. This condo is a great alternative to renting and a chance to build equity in one of Fairfield Cou

$285,000

2 beds1 bath860 sq ft

290 W Main St #4, Stamford, CT 06902

Elevated city views • $350 HOA • 2 parking spots

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Exquisite Stonington Estate. Set amidst 10.19 manicured acres of breathtaking privacy and natural beauty, the extraordinary Crossover Estate offers the very best of refined coastal living just moments from the charming Stonington Borough and Historic Downtown Mystic. The best of One-Level Living. This exceptional family compound is bordered by a tranquil pond and brook on one side, with a picturesque estuary leading to Long Island Sound on the other. Ideally positioned between Boston and New York City, and only minutes to Mystic, Watch Hill and the Mystic Amtrak station, this remarkable estate offers effortless access for both weekend escapes and year-round enjoyment. The best of one-level

$3,595,000

7 beds4.5 baths11,726 sq ft

455 Stonington Rd, Stonington, CT 06379

Custom cabinetry • Picturesque estuary • Tranquil pond

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Beautifully remodeled home in a highly desirable neighborhood. This move-in ready home features a bright, open floor plan with newly refinished hardwood floors, fresh paint, and a designer finish throughout. The stunning custom kitchen offers white shaker cabinetry, quartz countertops, a center island, and brand-new stainless steel appliances. Bathrooms have been completely renovated with gorgeous modern tile, designer finishes, and stylish fixtures. Additional updates include new trim, interior and exterior doors, hardware, and LED lighting throughout. The spacious primary suite features a stunning kitchenette, beautifully appointed private bath, and its own separate entrance making it ide

$469,800

4 beds2.5 baths1,885 sq ft

162 Forest St, Hamden, CT 06518

Custom kitchen • Open floor plan • Quartz countertops

ABOUT THIS HOME
Vintage Home for sale in Connecticut, CT:
Excellent opportunity to own a fully occupied two-family property offering immediate cash flow and long-term investment potential. Currently generating $3,900 per month in rental income, with one unit rented for $1,900/month and the other for $2,000/month, this property is a solid addition to any investment portfolio. Each unit features 2 bedrooms, with one offering 1 full bathroom and the other 1.5 bathrooms, providing comfortable and functional living spaces for tenants. With approximately 2,209 square feet of living space, this well-maintained multifamily offers plenty of room while delivering consistent rental income. Additional features include a detached garage ideal for storage, a la

$419,000

4 beds2.5 baths2,209 sq ft

45 Dunham St, Norwich, CT 06360

Large driveway • Public sewer • Two-family property

Property at 50 Albert Rd, Hamden, CT 06514, 3 beds, 1 bath

$325,000

3 beds1 bath1,075 sq ft

50 Albert Rd, Hamden, CT 06514

Property at 810 Lindley St, Bridgeport, CT 06606, 6 beds

$678,000

6 beds— baths2,194 sq ft

810 Lindley St, Bridgeport, CT 06606

Property at 572 Elm St, New Haven, CT 06511, 9 beds, 3 baths

$825,000

9 beds3 baths4,998 sq ft

572 Elm St, New Haven, CT 06511

Property at 111 Linwood St, New Britain, CT 06052, 4 beds, 2 baths

$350,000

4 beds2 baths1,438 sq ft

111 Linwood St, New Britain, CT 06052

Property at 65 S Main St, Jewett City, CT 06351, 7 beds, 4 baths

$769,000

7 beds4 baths8,000 sq ft

65 S Main St, Jewett City, CT 06351

Property at 837 Bank St, New London, CT 06320, 5 beds, 4 baths

$499,900

5 beds4 baths2,478 sq ft

837 Bank St, New London, CT 06320

Property at 61 Soap St, Dayville, CT 06241, 4 beds, 3 baths

$400,000

4 beds3 baths2,000 sq ft

61 Soap St, Dayville, CT 06241

Property at 26 Marsdale Ave, Bridgeport, CT 06606, 3 beds, 1.5 baths

$470,000

3 beds1.5 baths2,030 sq ft

26 Marsdale Ave, Bridgeport, CT 06606

Property at 63 Thompson St, Hamden, CT 06518, 4 beds, 2 baths

$329,000

4 beds2 baths1,163 sq ft

63 Thompson St, Hamden, CT 06518

Property at 15 Green St, Stafford Springs, CT 06076, 7 beds, 3 baths

$424,000

7 beds3 baths3,092 sq ft

15 Green St, Stafford Springs, CT 06076

Property at 326 Lake Shore Dr, Middlebury, CT 06762, 3 beds, 2 baths

$520,000

3 beds2 baths1,568 sq ft

326 Lake Shore Dr, Middlebury, CT 06762

Property at 849 Frost Rd, Waterbury, CT 06705, 5 beds, 2 baths

$549,995

5 beds2 baths1,668 sq ft

849 Frost Rd, Waterbury, CT 06705

Property at 1770 Stratfield Rd, Fairfield, CT 06825, 3 beds, 2 baths

$679,900

3 beds2 baths1,800 sq ft

1770 Stratfield Rd, Fairfield, CT 06825

Property at 40 Main St, Plainfield, CT 06374, 6 beds, 4.5 baths

$1,100,000

6 beds4.5 baths5,856 sq ft

40 Main St, Plainfield, CT 06374

Property at 1050 Whitney Ave, Hamden, CT 06517, 5 beds, 4.5 baths

$1,795,000

5 beds4.5 baths5,345 sq ft

1050 Whitney Ave, Hamden, CT 06517

Property at 15 Matson Ct, Waterbury, CT 06704, 6 beds, 3 baths

$489,000

6 beds3 baths4,003 sq ft

15 Matson Ct, Waterbury, CT 06704

Property at 163 Pearl St, Middletown, CT 06457, 6 beds, 2 baths

$410,000

6 beds2 baths2,982 sq ft

163 Pearl St, Middletown, CT 06457

Property at 44 Toms Rd, Stamford, CT 06902, 5 beds, 3.5 baths

$849,999

5 beds3.5 baths2,846 sq ft

44 Toms Rd, Stamford, CT 06902

Property at 115 Dewitt St, New Haven, CT 06519, 6 beds, 3.5 baths

$469,000

6 beds3.5 baths2,655 sq ft

115 Dewitt St, New Haven, CT 06519

Property at 3 Anchorage Ln, Old Saybrook, CT 06475, 4 beds, 3 baths

$849,900

4 beds3 baths2,496 sq ft

3 Anchorage Ln, Old Saybrook, CT 06475

Property at 24 Sunfield Cir, Waterbury, CT 06708, 3 beds, 1.5 baths

$349,995

3 beds1.5 baths1,493 sq ft

24 Sunfield Cir, Waterbury, CT 06708

Property at 52 Pond Meadow Rd, Ivoryton, CT 06442, 2 beds, 2 baths

$430,000

2 beds2 baths810 sq ft

52 Pond Meadow Rd, Ivoryton, CT 06442

Property at 25 N Forest Cir, West Haven, CT 06516, 2 beds, 2 baths

$499,500

2 beds2 baths2,114 sq ft

25 N Forest Cir, West Haven, CT 06516

Property at 244 Sherman Ave, New Haven, CT 06518, 6 beds, 4 baths

$499,900

6 beds4 baths4,090 sq ft

244 Sherman Ave, New Haven, CT 06518

Property at 552 Dixwell Ave, New Haven, CT 06511, 6 beds, 3 baths

$469,900

6 beds3 baths3,004 sq ft

552 Dixwell Ave, New Haven, CT 06511

Property at 110 Green Hill Ln, Cheshire, CT 06410, 5 beds, 2 baths

$450,000

5 beds2 baths1,584 sq ft

110 Green Hill Ln, Cheshire, CT 06410

Property at 50 Nash St, New Haven, CT 06511, 12 beds, 5 baths

$1,595,000

12 beds5 baths5,661 sq ft

50 Nash St, New Haven, CT 06511

Property at 295 Smith Hill Rd, Colebrook, CT 06021, 5 beds, 4.5 baths

$2,200,000

5 beds4.5 baths4,807 sq ft

295 Smith Hill Rd, Colebrook, CT 06021

Property at 52 Jackson Rd, Enfield, CT 06082, 3 beds, 1.5 baths

$339,900

3 beds1.5 baths1,372 sq ft

52 Jackson Rd, Enfield, CT 06082

Property at 82 S 2nd Ave, Taftville, CT 06380, 3 beds, 1 bath

$299,900

3 beds1 bath1,367 sq ft

82 S 2nd Ave, Taftville, CT 06380

Property at 445 Farmington Ave, Waterbury, CT 06710, 4 beds, 1.5 baths

$325,000

4 beds1.5 baths2,716 sq ft

445 Farmington Ave, Waterbury, CT 06710

Property at 51 Arnold Way #51, West Hartford, CT 06119, 2 beds, 1 bath

$265,000

2 beds1 bath896 sq ft

51 Arnold Way #51, West Hartford, CT 06119

Property at 88 Powder Hill Rd, Middlefield, CT 06455, 4 beds, 2.5 baths

$749,900

4 beds2.5 baths2,458 sq ft

88 Powder Hill Rd, Middlefield, CT 06455

Property at 937 New Britain Ave, West Hartford, CT 06110, 5 beds, 2 baths

$519,900

5 beds2 baths2,836 sq ft

937 New Britain Ave, West Hartford, CT 06110

Property at 9 Westchester Dr, Bristol, CT 06010, 3 beds, 1 bath

$279,888

3 beds1 bath768 sq ft

9 Westchester Dr, Bristol, CT 06010

Property at 3674 Park Ave, Bridgeport, CT 06604, 3 beds, 1 bath

$450,000

3 beds1 bath1,513 sq ft

3674 Park Ave, Bridgeport, CT 06604

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Based on information submitted to the MLS GRID as of Wed Sep 02 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Connecticut

There are currently 2614 vintage homes for sale in Connecticut. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. This map is refreshed with the newest listings in Connecticut every 15 minutes.

Find your dream vintage homes in Connecticut using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Connecticut are local experts and are ready to answer your questions about properties , neighborhoods, schools, and the newest listings for sale in Connecticut. If you're looking to sell your home in the Connecticut area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Connecticut with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

Vintage homes for sale & real estate in Connecticut, CT

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